East Bengal FC formed in 1920, played its centenary season, competing in the I-League, Durand Cup and Calcutta Football League.

East Bengal FC made the announcement of retaining core players of the 2018-19 I-League campaign for the next season starting with Brandon Vanlalremdika, Lalrindika Ralte, Borja Gomez and Samad Ali Mallick.

[10] On 8 June, controversy related to Jobby Justin newly emerged after the transfer saga to ATK was questionable and the AIFF passed the incident to the IFA disciplinary committee for their decision.

[14] On 26 June, East Bengal FC announced that assistant coach Bastob Roy will continue for the 2019–20 season and will also be the head of Youth Development.

forward Ronaldo Oliveira, who became the top scorer with 23 goals and SESA FA defender Anil Chavan, to join the trails and if they can impress coach Alejandro Menéndez, they will be signed.

[17] On 4 August, East Bengal FC confirmed that Goanese forward Ronaldo Oliveira has signed for the club on a 3 years contract after impressing the coaching staff in the trials.

[19] On 23 August, East Bengal FC completed their quota of foreigners as they announced the signing of Juan Mera Gonzalez from SD Leioa, who can play as a left-winger as well as attacking midfielder.

The Red and Gold brigade, however, rallied from behind in the second half with a brace from their academy graduate Bidyashagar Singh to win it 2–1 and top the group stages and enter the semi-finals.

Samad Ali Mallick scored the first goal for the Red and Gold brigade, however, Marcus Joseph made no mistakes as he equalized for the visiting side in the dying minutes of the match after Mehtab Singh conceded a penalty by pulling down Henry Kisekka, resulting in the former being sent-off.

10 men East Bengal FC took the match to the tie-breakers but Lalrindika Ralte, Jaime Santos Colado and Naorem Tondomba Singh missed from the spot as Gokulam Kerala F.C.

William Opoku reduced the margin in the dying minutes from a penalty which was conceded as the ball struck Kamalpreet Singh's hand inside the box.

Spanish striker Marcos de la Espada debuted in the match for the Red and Gold brigade and in the muddly playing conditions had a decent first outing.

next on 28 August in the Calcutta Football League at the East Bengal Ground and won quite handsomely by a 3–0 margin with Lalrindika Ralte opening the scoring in the 40th minute and Jaime Santos Colado netting a brace in the second half.

The Red and Gold brigade would have had a huge scoreline if not for the missed chances in the second half from Bidyashagar Singh, Samad Ali Mallick, Ronaldo Oliviera.

Coach Alejandro Menendez benched two top scorers Jaime Santos Colado and Bidyashagar Singh for the match, which ended in a goalless stalemate with both teams failing to break open the deadlock.

Kalighat MS reduced the margin in the 82nd min to make the scoreline 3–2 but East Bengal team was fast to react as Jaime Santos scored again within a minute to take full 3 points from the match.

in the next match of the 2019–20 CFL on 16 September at the Kalyani Stadium and in a tense game, the Red and Gold brigade twice went ahead, however, both times nullified by Bhawanipur to end 2–2.

[42] East Bengal FC faced their rivals Mohammedan Sporting in the next match of the 2019–20 CFL on 26 September at the Salt Lake Stadium and in a potential title decided the Red and Gold brigade edged past the Black Panthers by 3–2 scoreline.

Mohammedan Sporting was quick to react as they equalised in the 23rd min as Borja Gomez Perez deflected the ball into his own net from a setpiece movement.

In the 43rd min, East Bengal won a penalty after Shaiful Rahman stopped the ball with his hand as it was going into the goal, hence getting a red card in the process; Jaime Santos Colado did no mistake in scoring from the spot to take a 2–1 lead at HT.

East Bengal increased the lead in the second half as Marcos de la Espada tapped in from close range from a Lalrindika Ralte cross to make it 3–1.

[52] East Bengal FC will faced Churchill Brothers away on 4 January at the Fatorda Stadium and lost courtesy of a solitary goal in the 89th minute from Willis Plaza.

[57] On 21 January, just 2 days after the Kolkata Derby defeat, East Bengal FC announced that coach Alejandro Menendez had resigned from his position for personal reasons and taking responsibility if the poor performance of the team.

[58] On 22 January, the East Bengal FC management announced a double signing: Liberian striker Ansumana Kromah and Monotosh Chakladar for the remainder of the season.

[61] East Bengal FC faced Indian Arrows on 1 February at the Kalyani Stadium in the next match and lost by 1–0, courtesy of a solitary goal by Vikram Pratap Singh in the 58th minute.

East Bengal FC scored 4 goals in the second half courtesy of 4 different scorers: Jaime Santos Colado, Kassim Aidara, Brandon Vanlalremdika and Marcos de la Espada.

[67] East Bengal FC faced Churchill Brothers S.C. next on 29 February at the Salt Lake Stadium and in a fiercely competitive match managed to share points with a dying minute equalizer goal from Jaime Santos Colado to make it 1-1.

on 9 March at the TRC Turf Ground and won by a solitary penalty goal in the dying minutes of the injury time by Víctor Pérez Alonso to snatch all 3 points and move up to the 2nd place in the league table.

[71] East Bengal FC was supposed to face arch-rivals Mohun Bagan in the second leg of the Kolkata Derby next on 15 March at the Salt Lake Stadium however due to the outbreak of COVID-19, all matches of the 2019-20 I-League has been suspended till 14 April until further notice.

[72][73] On 18 April, due to the COVID-19 pandemic, the All India Football Federation announced that the remaining matches of 2019-20 I-League will be cancelled and Mohun Bagan was awarded as the champions.